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一个黄金机遇:奥酮类化合物的苯并呋喃酮修饰及其对光学性质、毒性和染料潜力的影响

A golden opportunity: benzofuranone modifications of aurones and their influence on optical properties, toxicity, and potential as dyes.

作者信息

Schmitt Joza, Handy Scott T

机构信息

Department of Chemistry, Middle Tennessee State University, Murfreesboro, TN 37132, USA.

出版信息

Beilstein J Org Chem. 2019 Jul 25;15:1781-1785. doi: 10.3762/bjoc.15.171. eCollection 2019.

DOI:10.3762/bjoc.15.171
PMID:31435449
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6664396/
Abstract

Aurones are a small subclass of the flavonoid family known primarily for their unusual structure and the golden yellow color they impart to the flowers of snapdragons and cosmos. Most studies of aurones focus on their range of biological activities, but relatively little has been reported with respect to their optical properties, unlike their aza and thio analogs. What little is known has focused entirely on the influence of the benzylidene portion. In this study, the influence of substitution in the benzofuranone ring on the UV-vis spectrum is explored, as well as an initial screening of their toxicity and a qualitative preliminary study of their potential to act as fabric dyes.

摘要

噢哢类化合物是黄酮类家族中的一个小亚类,主要因其独特的结构以及它们赋予金鱼草和大波斯菊花朵的金黄色而闻名。大多数关于噢哢类化合物的研究都集中在它们的一系列生物活性上,但与它们的氮杂和硫代类似物不同,关于它们光学性质的报道相对较少。目前已知的少量信息完全集中在亚苄基部分的影响上。在本研究中,探索了苯并呋喃酮环上的取代对紫外可见光谱的影响,以及对它们毒性的初步筛选和对它们作为织物染料潜力的定性初步研究。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24fd/6664396/cb8138e7460b/Beilstein_J_Org_Chem-15-1781-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24fd/6664396/e7169eb2a69e/Beilstein_J_Org_Chem-15-1781-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24fd/6664396/d42748307cf6/Beilstein_J_Org_Chem-15-1781-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24fd/6664396/9678e7d48a7a/Beilstein_J_Org_Chem-15-1781-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24fd/6664396/cb8138e7460b/Beilstein_J_Org_Chem-15-1781-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24fd/6664396/e7169eb2a69e/Beilstein_J_Org_Chem-15-1781-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24fd/6664396/d42748307cf6/Beilstein_J_Org_Chem-15-1781-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24fd/6664396/9678e7d48a7a/Beilstein_J_Org_Chem-15-1781-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24fd/6664396/cb8138e7460b/Beilstein_J_Org_Chem-15-1781-g005.jpg

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J Fluoresc. 2025 Mar;35(3):1573-1597. doi: 10.1007/s10895-024-03607-x. Epub 2024 Feb 27.
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本文引用的文献

1
Fluorescence properties of aurone derivatives: an experimental and theoretical study with some preliminary biological applications.
Photochem Photobiol Sci. 2017 Aug 9;16(8):1268-1276. doi: 10.1039/c7pp00078b.
2
Natural Colorants: Historical, Processing and Sustainable Prospects.天然色素:历史、加工与可持续发展前景
Nat Prod Bioprospect. 2017 Feb;7(1):123-145. doi: 10.1007/s13659-017-0119-9. Epub 2017 Jan 16.
3
Aurones: interesting natural and synthetic compounds with emerging biological potential.噢哢类化合物:具有新出现生物学潜力的有趣天然及合成化合物。
Nat Prod Commun. 2012 Mar;7(3):389-94.
4
Recent advances in the medicinal chemistry of aurones.奥罗宁类化合物的药物化学研究进展。
Curr Med Chem. 2012;19(18):2861-75. doi: 10.2174/092986712800672085.
5
Aurones: small molecule visible range fluorescent probes suitable for biomacromolecules.查耳酮:小分子可见范围荧光探针,适用于生物大分子。
J Fluoresc. 2011 Nov;21(6):2173-84. doi: 10.1007/s10895-011-0919-y. Epub 2011 Jul 12.
6
Functionalized aurones as inducers of NAD(P)H:quinone oxidoreductase 1 that activate AhR/XRE and Nrf2/ARE signaling pathways: synthesis, evaluation and SAR.功能化奥瑞因作为 NAD(P)H:醌氧化还原酶 1 的诱导剂,激活 AhR/XRE 和 Nrf2/ARE 信号通路:合成、评价和 SAR。
Eur J Med Chem. 2010 Jul;45(7):2957-71. doi: 10.1016/j.ejmech.2010.03.023. Epub 2010 Mar 25.